Enterprise Account Executive

Wingspan serves independent contractors and the businesses that hire them. Our customers are the backbone of the modern economy and are radically underserved by legacy payroll platforms. Our job is to make working with them effortless.

Wingspan is the first payroll platform built specifically for the independent workforce. We're different because of our end-to-end contractor management: seamless onboarding, automated payments, and built-in compliance, all in one place, for flexible workforces of any size. That's why the businesses that rely on contractors trust Wingspan to handle the complexity so they don't have to.

This market is massive and ours to define. By 2027, half the U.S. workforce will be independent contractors, and we're the system of record they've never had. We're a Series B company backed by Andreessen Horowitz (a16z) and the founders and CEOs of Warby Parker, Harry's, Allbirds, Invision, and Flatiron Health.

This is a 0-to-1 role. As our first Enterprise AE, you'll own the full sales lifecycle, build the playbook alongside the CEO, and work hand-in-hand with Product and Engineering to make sure we're delivering for our largest customers. There's no inherited process or predefined territory, you'll be the one defining how Wingspan wins in the enterprise market. If you're the type of seller who'd rather architect something than inherit it, this role is for you.

• →Own the full-cycle sales lifecycle for enterprise accounts, from prospecting to closing
• →Close six-figure+ ARR deals
• →Lead multi-threaded discovery, exec-level conversations, and longer sales cycles
• →Help build out our enterprise sales playbook, collaborating closely with the CEO
• →Source a portion of your own pipeline through strategic personalized outreach campaigns
• →Build a strong relationship with our marketing team to better our demand generation efforts and selling materials 
• →Travel as needed to cultivate industry and prospect relationships, typically once per month
• →Be the face of our brand, pairing genuine customer empathy with sharp, methodical problem-solving, while building deep credibility with finance and accounting buyers.

• You have 3+ years of experience in an enterprise SaaS sales role, with a track record of exceeding targets and closing six-figure+ ARR deals
• You have experience being one of the earliest salespeople at a startup or building out a new vertical or product at a larger company. 
• You are a self-starter and thrive in and are excited by an ambiguous environment where you can build something from 0-1
• You become an expert in your domain, always seeking to deepen your understanding of the industry and prospects you sell to 
• You are based in NYC or willing to relocate and value the collaboration of building something great together in person
• You collaborate and build relationships internally, from marketing to product, providing insights to better our product and demand generation campaigns
• You have sold into scaling startups and tech companies

• This role will be based in New York City and will have a hybrid work model that consists of a combination of onsite (3 days per week) and remote work expectations. This model is designed to provide our employees with an optimal balance between in-person collaboration and the convenience of remote work. We believe this approach fosters a more productive and engaging work environment while supporting our commitment to employee well-being and work-life balance. 
• Please note that the specific onsite and remote work schedule will be established based on the requirements of the role and the needs of the organization, and remain subject to Company discretion.  The Company reserves the right to modify its in-person and remote work policies and expectations.